The Upgrade, Episode 2: getting real answers out of your guest data

A recap from Jesse, Director of Product at Bookboost

Last week, Jamie and I sat down for episode two of The Upgrade. Episode one was a broad sweep of everything we shipped in Q1. This time we went deep on one thing, the one that generated the most follow-up questions last time round: Bookboost Insights.

I am a data analyst and engineer by trade, so this is the episode I have been quietly waiting to do. I also took on a live demo, on a live webinar, which is its own special form of courage. Here is the recap, with a few notes from my side of the screen.

The problem we kept running into

Jamie opened with a poll result from episode one. We had asked the audience how they report on guest engagement today, and the answers were telling:

• 31% do not report on it at all
• 31% rely on basic PMS reports
• 19% stitch it together across spreadsheets
• 19% have a proper BI tool in place

So more than 80% are either flying blind, rebuilding the same answer from scratch every time, or gluing it together by hand.

Here is the thing that makes this almost funny. Hotels are not short on data. It is everywhere. PMS, channel manager, booking engine, inbox, email tools, review platforms, I could keep going. The problem is not that the data is missing. The problem is that data does not speak to itself.

A guest profile in the PMS is siloed away. It does not know that the same guest opened your marketing campaign. A reservation has no idea what that guest was asking on WhatsApp the night before check-in. We live in a paradigm where we have more information than any time in human history, and we spend 99% of our time gathering it instead of using it to make a decision.

Why it stays difficult

When a hotelier actually wants to answer a question properly today, it usually goes one of two ways:

1. You live in spreadsheets, pulling data together, and it eats your entire week.
2. You invest in a data and BI stack: a data engineer, a data analyst, tooling licences. For most hotels, and most hotel groups, that maths simply does not work out.

So people default to the spreadsheet, or they stop asking the question altogether.

And even the teams who have a BI tool tell me they are still stuck. The marketing manager has to ask the data person, the data person is busy, and by the time the answer comes back the moment has passed. I have been on both sides of that queue, as the asker and the answerer. Most hoteliers are not data engineers, and they should not have to be. Nobody should need Python or SQL to ask a simple question about their own guests. If that is the price of entry, the data may as well not exist, because it never gets put to work.

Where Insights actually came from

Every good origin story starts with a real customer, and this one does too.

We were running a proof of concept with CIC Hospitality, a fantastic customer of ours up in the Nordics, and we were struggling to show the value of our unified inbox in a way that was easy to consume. So Celia, one of our customer success managers, did the thing every data-obsessed person will recognise instantly. She opened the inbox and worked through the tickets one by one in an Excel spreadsheet until she spotted a pattern.

The pattern was the airport shuttle. Guests kept asking the same questions, over and over: what time, how often, where it left from, where it arrived. So the team updated their OTA listings, which had none of that information, and improved their pre-arrival messaging in the Bookboost CRM. The repeat questions tailed off and disappeared.

That was the moment it clicked for us. The signal is in the data. We have everything we need to make these discoveries, but someone has to go and find it. Celia's manual ticket-by-ticket analysis became the seed of the inbox dashboard in Insights. The difference is that what took her an afternoon now takes seconds with an AI summary, and anyone can do it.

What it grew into

Bookboost Insights is a native analytics layer built on top of the Bookboost CDP. A few things to know:

• Three ready-made dashboards, curated by our team and design partners, covering the unified inbox, marketing, and reservations.
• Custom dashboards you build yourself to answer your own questions.
• AI summaries that read the data and tell you what is happening in plain language.
• Insights agents you can ask anything in plain English, and get the analysis back.
• Scheduling and delivery: export to CSV or image, send via email, SFTP, S3, or webhook.

No separate BI tool. No data team. Everything you would otherwise build yourself, already built and already connected to your guest data.

The demo, in two pairs of shoes

Rather than talk about it, I put my feet in two roles and showed it live.

The marketing manager wanted to dig into campaign open rates. I gave the insights agent a single plain-English prompt and let it choose its own data model. It queried the active campaigns, calculated averages, standard deviation and a Z score to flag anomalies, visualised the result, and summarised it, surfacing the one statistically significant underperformer and why. Then came the dreaded follow-up question, the one that usually breaks everything: forget open rates, show me click-through. A new direction, answered in seconds. No SQL, no data team, no three-day wait on a ticket.

The commercial manager was prepping for a meeting with a GM on property. We compared direct versus OTA performance: reservations, revenue, ADR, length of stay, occupancy. Useful, but standard PMS territory. Where Insights really earns its keep is that the CDP underneath connects every reservation to the human who made it. So I went deeper: which nationalities visit most often, and how does loyalty adoption differ between them? The agent combined guest profiles, loyalty data and reservations and pointed straight at an opportunity, a large group of Swedish guests with only moderate loyalty uptake. The obvious next move: translate the loyalty programme into Swedish and market it there.

Then I took that chart into the dashboard builder, recoloured it to our purple because we love purple, added an AI summary, and in a few steps had something I could share with the team. From a sentence of natural language to a shareable dashboard.

Once you are at a dashboard, the options open up. Schedule it, in whole or in parts. Alert on a metric so the dashboard works for you instead of the other way round. Share it with colleagues and collaborate in one workspace. And because Insights is really your view into the CDP, you can pipe that pre-transformed data out via SFTP, S3 or webhook to enrich a data platform you have already built. Insights does not have to replace what you have. It can feed it.

The questions you asked

"We run multiple properties across different brands. Can we roll up at group level but still drill down per hotel?"

Yes. Every data model in Insights is built at the organisation level, which is your group level, but we keep the relationships down to each individual property intact. We use this ourselves at Bookboost to see how our whole portfolio is performing ahead of quarterly business reviews. There are filters on dashboards, and drag-and-drop property-by-property breakdowns. The part I find genuinely exciting is using the agent to compare properties directly: here is hotel A, here is hotel B, B is underperforming, what is different? That kind of comparison used to take forever. Now it does not.

"What are customers actually using Insights for?"

The use case that stands out for me has come up with two customers in the past couple of months, both building loyalty programmes from scratch and using Insights as a co-pilot. They are asking how to bucket their loyalty tiers based on their actual guest data. This is where the CDP matters: our data survives migration. We have customers who have moved across three different PMS platforms over nine years. You cannot design a loyalty programme off eighteen months of data, and with Insights we can look back across all nine years and all three migrations to help shape the tiers and incentives.

I love that this came up organically. It is early days, and I suspect we will be doing this episode again in a few months with a longer list.

What's next

Insights is in early access right now, and we would genuinely love more hoteliers in the cohort. You can also watch episode two on demand any time, to see the full session and the live demo for yourself.

If you are already a Bookboost customer and want in, register for Insights early access or reply to any of our follow-up emails. If you are not yet, and you want to see how Insights sits on top of the CDP and CRM, we are happy to walk you through the whole platform in context.

Thanks to everyone who joined, asked a question, or said hello in the chat. We are proud of what we have built here, and it is far more fun to show it than to talk about it.

See you in the next episode.

Jesse

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